The instant invention relates to 1,1,4,7-tetramethyl-3-indanone defined according to the structure: ##STR2## a process for preparing same and uses of same in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
Inexpensive chemical compounds which can provide ambery, leathery, wood, fig-like and honey aromas with tobacoo and hay-like topnotes are highly desirable in the art of perfumery. Many of the natural materials which provide such fragrances and contribute such desired nuances to perfumery compositions are high in cost, unobtainable at times, vary in quality from one batch to another and/or are generally subject to the usual variations of natural products.
There is, accordingly, a continuing effort to fine synthetic materials which will replace, enhance or augment the fragrance notes provided by natural essential oils or compositions thereof. Unfortunately, many of the synthetic materials either have the desired nuances only to a relatively small degree or they contribute undesirable or unwanted odor to the compositions.
Bicyclic ketones are known for use in perfumery in the prior art. Thus, Arctander, "Perfume and Flavor Chemicals (Aroma Chemicals)" 1969, at monograph number 1791 and U.S. Pat. No. 2,912,462 issued on Nov. 10, 1959 discloses the compound having the structure: ##STR3## as having a dry, woody, amber-like and somewhat orris-like aroma. The compound having the structure: ##STR4## is commercially sold as "KETONE BD-9".
The compound having the structure: ##STR5## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond is disclosed as being useful in perfumery (having a wood or ambergris aroma) in Japanese Published Patent No. 57-53768 assigned to the Takasago Perfumery Company.
The compound having the structure: ##STR6## is disclosed as being useful in perfumery in U.S. Pat. No. 3,847,993 issued on Nov. 12, 1974. This compound is indicated to be produced using the compound having the structure: ##STR7## as a precursor according to the reaction: ##STR8##
The compound having the structure: ##STR9## is disclosed as being useful in perfumery by Ferrero and Heig, Helv. Chim. Act. Volume XVII, Fasc. VI (1959) Number 228 at page 2111. This compound having the structure: ##STR10## is produced from the compound having the structure: ##STR11## which is indicated to be an intermediate. Furthermore, in Ferrero and Heig, the compound having the structure: ##STR12## is indicated to be an intermediate for producing acylated indanes from the compound having the structure: ##STR13## The compound having the structure: ##STR14## is indicated as compound XXIX. The compound having the structure: ##STR15## is indicated as compound XXVIII in Example C-3 at page 2119 of Ferrero and Heig.
Furthermore, the reaction: ##STR16## wherein R is lower alkyl such as methyl is disclosed in U.S. Pat. No. 3,078,319 issued on Feb. 19, 1963 wherein it is indicated that the resulting indanes may be acylated.
In addition, the use of cobalt acetate bromide and oxygen for the production of ketones is shown by Hay, et al, in the Canadian Journal of Chemistry, 43,1306 (1965). In this process, tetralin is oxidized to the corresponding ketone, that is .alpha.-tetralone.
Nothing in the prior art, however, indicates the unexpected, unobvious and advantageous properties of the 1,1,4,7-tetramethyl-3-indanone having the structure: ##STR17## Furthermore, nothing in the prior art describes the process for preparing such 1,1,4,7-tetramethyl-3-indanone according to the reaction sequence: ##STR18##